I was in my late 20's and me and my girlfriends thought that we were all that, a little on the egotistical side now that I look back on it.
I was always getting compliments about my figure, I was a tall blonde with long legs that some people thought I should be a model. I was probably about 20 pounds lighter then, wore a size small for underwear and a 36C bra. I did love to show off my curves.
At that point in my life I had a few boyfriends and a couple of one night stands but I wouldn't consider myself experienced or an expert at sex. I had did a lot of experimenting but I think the naughtiest thing I had done was give a guy a blowjob with his parents in the next room.
A few of us were out one day in a part of town that we don't usually go to looking for a new place to rent. The place we looked at was quite reasonably priced but we weren't sure of the location so we decided to check out the amenities.
Eventually we ended up at a lounge to discuss if we wanted to take the place or not. It was okay, not very busy as it was just after supper and before the night crowd may their way in.
There wasn't a waitress around so I went to the bar to get us some drinks. An old man was sitting at the bar sipping on a martini. I got the bartender's attention and ordered our drinks.
The man sitting at the bar said "You are a very lovely young lady, very beautiful."
"Thank-you, very kind," I responded hoping that was the end of the conversation but I saw him looking at my legs and the length of my skirt that was well above my knees, if he did speak to me again I was expecting him to tell me to put some clothes on that fit or something else.
"You probably get a lot of attention from men don't you honey?"
"I guess I catch the eye of my share of guys."
"I bet you do, but do you know why none of them will satisfy you?"
I wasn't about to take love advice from someone who was as old as he was and likely hadn't been in the dating scene for like 100 years so I collected our drinks and headed back to the table.
"You aren't even a little bit curious honey?"He called after me.
Shit, I am very curious what he has to say, goddamn old man. I put the drinks on the table and headed back to where the old guy was sitting. I pulled the bar stool out beside him and sat down making sure my legs were firmly crossed.
"So..." I was going to address him but I didn't know his name!
"Henry, my dear, my name is Henry."
"Okay Henry, my name is Christy, why don't you tell me why none of the men will satisfy me?"
He put a hand on my knee and set his martini down and said "Well dear, it is really quite simple: men of this generation simply don't care if a woman enjoys sex they just want to have sex with as many as they can, sort of keep score of their conquests."
Now he got me thinking about my past sexual experiences, he did have a point in most cases, maybe all cases, the guy didn't spend a lot of time making me cum but just wanting to cuck me. I looked down at his hand on my knee, it was steady, not nervous at all, hmm that's different, most men who touch my leg are rubbing it not keeping it in one spot.
"And it was different for men from your generation, Henry?"
"Oh yes, we took care of our women first and foremost, put them on a pedestal and as a result, sex was much better."
"Then you can satisfy your wife the same you could when you were first together?"
"My wife passed about 8 years ago from cancer, but yes I can still satisfy a woman as I could when I was your age."
"I'm sorry Henry about your wife I didn't know."
"Of course, how could you, dear, how old do you think I am?"
I'm looking at him and start to think to myself he must be well over 70, "I'm not very good at this game but I will say 73."
"You're not far off, I am 68 years young, and how about you?"
"I am 27."
"Well dear, I'm going to guess that you have had a few boyfriends, but none of them made you orgasm, did they?"
"I'm not comfortable discussing this with you, but yes they did, well some of them did at least."
"What if I told you I could make you orgasm without you taking any of your clothes off and me not touching anything that is covered by your clothes?"
"Really, you can do that?" I said mostly sarcastically.
"Yes I can, are you interested?"
"I'm not sure yet. And what if you can't?"
"Then I will treat you and your friends to a wonderful dinner here and pay for your drinks."
"Okay but what if you can?"
"Then you will let me show you how a man is supposed to please a woman and teach you how a gentleman performs in bed."
"Don't take this the wrong way, but..."
"Yes I can still get it up, my parts work very well dear, no worries there. I live close by, your friends can wait outside if they like."
I can't believe I am thinking about this, here is a guy who is practically old enough to be my grandfather and I'm considering having sex with him?
I tell him to wait while I talk to my friends. I go back to the table and tell my friends about it and they say it is up to me but they like the idea of free dinner and drinks.
I get up and walk back to the bar. "Well Henry you've got yourself a deal!"
He leads me to his car and a short drive later we arrive at a nice, mature house.
He gets out and opens the door for me, quite the gentleman.
We enter the house and he leads me to a bedroom, obviously not the master bedroom as it is small size but it is clean and cozy, I sit down on the bed.
"Okay dear, are you ready for me to begin?"
"Sure, go ahead."
"Okay, close your eyes and clear your mind"
I do as he says and I feel him sit down beside me. He moves my hair away from my neck and starts to kiss it. It feels good but nothing that is really stimulating. Then he starts to bite it, huh that feels really nice and I feel goosebumps start to form. He moves his mouth to my ears and is nibbling on them, that's a new one, more goosebumps and I feel my nipples harden and wetness between my legs, he is starting to get me very aroused. He moves around to the other side and repeats what he did on the first side, extra time biting my neck, it feels really good and for the first time I think he might make me orgasm fully clothed.
He kneels on the floor in front of me and asks me to uncross my legs, I do. I am aware that my skirt is high on my leg, like not covering much of anything, I'm sure he can see my underwear and likely how wet they are already.
He lifts one leg and puts it on his own leg and removes my shoe and then does the same for the other. He slides my bare foot onto his cock, wow he has some size to him I think and try to wiggle my toes to feel more of it. He is now caressing my foot on his cock, I feel my excitement level jump higher and when he grips the bottom of my foot I let out a moan, holy shit does that ever feel good. He moves his hand up my leg and is sort of massaging the calf, not sure what the method is but it is making me even wetter. He moves the foot resting on his cock to his shoulder and replaces it with my other foot, removes that shoe and rubs his cock with my foot. Back to massaging the calf, I can't believe how good that feels, I want to touch myself but I am still fully clothed. I can feel his cock is hard now but I don't get to enjoy it for long as he puts my leg up on his shoulder like the other.
He has a clear view up my dress but it doesn't distract him from his work, he uses both hands up one leg to the bottom of my dress, back down and then the same on the other leg. My god the pleasure when he gets to my upper thigh, his touch is not like anything I have ever experienced before. I am on the brink of cumming from this and then he asks me to stand up. I plant my feet on the ground, a little wobbly but I am back on my feet.
He moves around to be behind me and asks me to put my hands on the back of his head and to put my head down. I can pretty much see down my own dress now, nipples are very hard and my pussy is so wet, but what is he going to do here?
He rubs my arms with both hands, one arm at a time and when he hits my armpit it sends waves of pleasure throughout my body. Wait, is that an erogenous zone? Then I feel him do the same to the other side, shit it is that feels incredible. I am moaning quite loudly now and he continues working my arms and then starts a sort of massage of my armpits simultaneously and I feel an orgasm building, not quite there yet, then he bites the back of my neck sending pleasure waves throughout my body, he bites me again, another moan, then he starts sucking the back of my neck, I am moaning uncontrollable, followed by a bite and that's it I cum and cum and cum.